Tags

Type your tag names separated by a space and hit enter

Catalytic enantioselective construction of all-carbon quaternary stereocenters: synthetic and mechanistic studies of the C-acylation of silyl ketene acetals.
J Am Chem Soc. 2005 Apr 20; 127(15):5604-7.JA

Abstract

With the aid of an appropriate chiral catalyst, acyclic silyl ketene acetals react with anhydrides to furnish 1,3-dicarbonyl compounds that bear all-carbon quaternary stereocenters in good ee and yield. Mechanistic studies provide strong support for a catalytic cycle that involves activation of both the electrophile (anhydride --> acylpyridinium) and the nucleophile (silyl ketene acetal --> enolate).

Authors+Show Affiliations

Mermerian AH
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Fu GC
No affiliation info available

MeSH

AcetalsAcylationAnhydridesCatalysisEthylenesKetonesPyridinium CompoundsSilanesStereoisomerism

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.
Research Support, U.S. Gov't, P.H.S.

Language

eng

PubMed ID

15826199

Citation

Mermerian, Ara H., and Gregory C. Fu. "Catalytic Enantioselective Construction of All-carbon Quaternary Stereocenters: Synthetic and Mechanistic Studies of the C-acylation of Silyl Ketene Acetals." Journal of the American Chemical Society, vol. 127, no. 15, 2005, pp. 5604-7.
Mermerian AH, Fu GC. Catalytic enantioselective construction of all-carbon quaternary stereocenters: synthetic and mechanistic studies of the C-acylation of silyl ketene acetals. J Am Chem Soc. 2005;127(15):5604-7.
Mermerian, A. H., & Fu, G. C. (2005). Catalytic enantioselective construction of all-carbon quaternary stereocenters: synthetic and mechanistic studies of the C-acylation of silyl ketene acetals. Journal of the American Chemical Society, 127(15), 5604-7.
Mermerian AH, Fu GC. Catalytic Enantioselective Construction of All-carbon Quaternary Stereocenters: Synthetic and Mechanistic Studies of the C-acylation of Silyl Ketene Acetals. J Am Chem Soc. 2005 Apr 20;127(15):5604-7. PubMed PMID: 15826199.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Catalytic enantioselective construction of all-carbon quaternary stereocenters: synthetic and mechanistic studies of the C-acylation of silyl ketene acetals. AU - Mermerian,Ara H, AU - Fu,Gregory C, PY - 2005/4/14/pubmed PY - 2005/6/21/medline PY - 2005/4/14/entrez SP - 5604 EP - 7 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 127 IS - 15 N2 - With the aid of an appropriate chiral catalyst, acyclic silyl ketene acetals react with anhydrides to furnish 1,3-dicarbonyl compounds that bear all-carbon quaternary stereocenters in good ee and yield. Mechanistic studies provide strong support for a catalytic cycle that involves activation of both the electrophile (anhydride --> acylpyridinium) and the nucleophile (silyl ketene acetal --> enolate). SN - 0002-7863 UR - https://www.unboundmedicine.com/medline/citation/15826199/Catalytic_enantioselective_construction_of_all_carbon_quaternary_stereocenters:_synthetic_and_mechanistic_studies_of_the_C_acylation_of_silyl_ketene_acetals_ DB - PRIME DP - Unbound Medicine ER -